(1R,2R)-N-isopropyl-N'-phthaloyl-1,2-diphenylethylenediamine | 1558718-49-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (1R,2R)-N-isopropyl-N'-phthaloyl-1,2-diphenylethylenediamine
• CAS: 1558718-49-2
• 化学式: C₂₅H₂₄N₂O₂
• 分子量: 384.478
• InChiKey: OVOVPLZSKXFSCY-DHIUTWEWSA-N

物化性质

• 熔点：
  126-127 °C
• 沸点：
  531.4±50.0 °C(predicted)
• 密度：
  1.207±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  49.41
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1R,2R)-N-isopropyl-N'-phthaloyl-1,2-diphenylethylenediamine 在 一水合肼 作用下， 以 乙醇 为溶剂， 以508 mg的产率得到(1R,2R)-N-isopropyl-1,2-diphenyl ethylenediamine
  参考文献：
  名称：

  Chiral thiophosphoramide catalyzed asymmetric aryl transfer reactions for the synthesis of functional diarylmethanols

  摘要：

  In this investigation, chiral thiophosphoramide 3d was easily prepared from chiral (1R,2R)-1,2-diphenylethylenediamine and then applied as an efficient chiral ligand in the catalytic asymmetric arylation reactions of various aromatic aldehydes. The corresponding diarylmethanol products were produced with good to excellent yields (up to 98%) and enantioselectivities (up to 94%). The recovery of chiral ligand 3d could be as high as 96%. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.11.011
• 作为产物：
  描述：

  在 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 (1R,2R)-N-isopropyl-N'-phthaloyl-1,2-diphenylethylenediamine
  参考文献：
  名称：

  Enantioselectivity switch controlled by N,N′-di- or N,N,N′,N′-tetra-substituted chiral thiophosphorodiamide ligands, structural relatives of thioureas, in catalytic additions of diethylzinc to aldehydes

  摘要：

  We have developed a series of new chiral thiophosphorodiamide ligands derived from (1R,2R)-(+)-1,2-diphenylethylenediamine, which are the structural relatives of thioureas. An investigation into their catalytic properties in asymmetric additions of diethylzinc to aldehydes has shown that N,N,N',N'-tetra-substituted chiral thiophosphorodiamides can give (R)-secondary alcohols with up to 98% yield and 98% ee, while N,N'-di-substituted chiral thiophosphorodiamides give (S)-secondary alcohols with up to 99% yield and 97% ee values. The enantioselectivity switch is highly efficient with a broad substrate scope. We have also proposed hypothetical reaction pathways, which result in an enantioselectivity switch. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.12.014